Ambroxol

Absorption

Rapid and almost complete.

Description

Ambroxol HCl (18683-91-5) is a radical scavenger with anti-inflammatory activity. Blocks the generation of reactive oxygen species by bronchoalveolar lavage cells, inhibits doxorubicin-induced lipid peroxidation (70 mg/kg in rat), and inhibits the release of inflammatory mediators from human leukocytes and mast cells (effective dose ~ 100 μM)

Description

Ambroxol is a secretolytic agent (expectorant) that was developed by Boehringer-Ingelheim in the late 1960s and 1970s and commercialized in 1978. It is used to treat bronchopulmonary diseases by clearing mucus from the lungs. It is marketed under several trade names, often as the active ingredient in cough syrups.
Earlier this year, Daniel H. Geschwind and colleagues at UCLA discovered?an?exciting potential new use for ambroxol. They were searching for a way to allow the body to regenerate nerve cells in the central nervous system similarly to the way it spontaneously regrows cells in the peripheral nervous system (PNS).
By using bioinformatics techniques, the researchers identified a gene network used by the PNS to initiate self-repair. They then matched the expression patterns of genes in the network to a database of bioactive molecules that trigger the same patterns.
Out popped ambroxol! When the drug was fed to mice with optic nerve lesions, some neuron growth ensued. The authors believe that this finding “provides a functional genomics foundation for understanding neural repair and proof of the power of such approaches in tackling complex problems in nervous system biology”.

Originator

Mucosolvan,Thomae,W. Germany,1980

The Uses of Ambroxol

Ambroxol is a metabolite of Bromohexine. Ambroxol Hydrochloride is a bronchosecretolytic drug. Free base of Ambroxol Hydrochloride (A575900).

The Uses of Ambroxol

expectorant

Indications

Ambroxol is indicated for secretolytic therapy in bronchoplmonary disease with abnormal mucus secretion and transport. It allows the mucus to be more easily cleared and ease a patient's breathing.

Background

Ambroxol is a secretolytic agent used in the treatment of respiratory diseases associated with viscid or excessive mucus. It is the active ingredient of Mucosolvan, Lasolvan or Mucoangin. The substance is a mucoactive drug with several properties including secretolytic and secretomotoric actions that restore the physiological clearance mechanisms of the respiratory tract which play an important role in the body’s natural defence mechanisms. It stimulates synthesis and release of surfactant by type II pneumocytes. Surfactants acts as an anti-glue factor by reducing the adhesion of mucus to the bronchial wall, in improving its transport and in providing protection against infection and irritating agents.

Definition

ChEBI: Ambroxol is an aromatic amine.

Manufacturing Process

6.5 g of N-(trans-p-hydroxycyclohexyl)-(2-aminobenzyl)-amine were dissolved in a mixture of 80 cc of glacial acetic acid and 20 cc of water, and then 9.6 g of bromine were added dropwise at room temperature while stirring the solution. After all of the bromine had been added, the reaction mixture was stirred for two hours more and was then concentrated in a water aspirator vacuum. The residue was taken up in 2 N ammonia, the solution was extracted several times with chloroform, and the organic extract solutions were combined and evaporated. The residue, raw N-(trans-phydroxycyclohexyl)-( 2-amino-3,5-dibromobenzyl)-amine, was purified with chloroform and ethyl acetate over silica gel in a chromatographic column, the purified product was dissolved in a mixture of ethanol and ether, and the solution was acidified with concentrated hydrochloric acid. The precipitate formed thereby was collected and recrystallized from ethanol and ether, yielding N-(trans-p-hydroxycyclohexyl)-(2-amino-3,5-dibromobenzyl)-amine hydrochloride, MP 233-234.5°C (decomposition).

Therapeutic Function

Expectorant

Metabolism

Not Available

References

1) Teramoto et al. (1999), Effects of ambroxol on spontaneous or stimulated generation of reactive oxygen species by bronchoalveolar lavage cells harvested from patients with or without chronic obstructive pulmonary diseases; Pharmacology, 59 135 2) Nowak et al. (1995), Ambroxol inhibits doxorubicin-induced lipid peroxidation in heart of mice; Free Radic. Biol. Med., 19 659 3) Gibbs et al. (1999), Ambroxol inhibits the release of histamine, leukotrienes and cytokines from human leukocytes and mast cells; Inflamm. Res., 48 86